反応 #6102

ord-021666c894ee4cbba7a64470dd7059e7

反応方程式

N#Cc1ccccc1S
2-mercaptobenzonitrile
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide
→
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2C#N)SC[C@H]1OC(C)=O
expected product
収率 60.0%
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](Sc2ccccc2C#N)SC[C@H]1OC(C)=O
2-cyanophenyl 2,3,4-tri-O-acetyl-1,5-dithio-β-D-xylopyranoside
収率 60.0%

反応物

—
IV
N#Cc1ccccc1S
2-mercaptobenzonitrile
CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@@H](Br)SC[C@H]1OC(C)=O
2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide

試薬

[O-2].[Zn+2]
zinc oxide

反応条件

詳細条件
See reaction.notes.procedure_details.

実験手順

If the procedure described in Preparation IV is followed starting from 10.7 g (79.2.10-3 mol) of 2-mercaptobenzonitrile, 30.2 g (85.10-3 mol) of 2,3,4-tri-O-acetyl-5-thio-α-D-xylopyranosyl bromide and 6.3 g (77.4.10-3 mol) of zinc oxide (ZnO), 19.3 g (yield: 60%) of the expected product are obtained after crystallization from ether.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US05246961uspto-grants-1993_09